Nitrobenzyl ethers



Patented Feb. 26, 1952 UNITED STATES, PATENT OFFlCE NITROBENZYL ETHERS Saul R. Buc and David LRandall, Easton, Pa.,

assignors to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware r No Drawing. Application November 22, 1949, Serial No. 128,918

g 1 7 Claims. (01. 260-611) g This invention relates to nitrobenzyl others to be 190 parts or 92.5% for CsHnNOi. The of alcohols and alcohol ethers of p lyhydric alcoweight of the elements are theoretically :54.82,

hols and to methods for preparing these com- H=5.62, N=7.10 and an analysis showed pounds. 0:54.89, H=5.53 and N=7.03.

More particularly, the invention is directed to The reaction may be represented as follows: compounds having the following general formula: NO2

NO; x

+HOCHCHOE 10 CHzCl wherein R is the ether residue formed from compounds selected from the group consisting of alcohol and alcohol ethers of polyhydric alcol6 C O hols, X is selected from the igroup consisting of w HIGH-FE 1 hydrogen and methyl, and Y is selected from the Example H group consisting of hydrogen, chlorine and the methyl ethers of alcohols and alcohol ethers of The process 0f E a p Was repeated using polyhydric alcohols. 514.5 parts by weight of nitrobenzyl chloride and In copending applications Serial Nos. 128,916, parts by weight f thylene g c c u filed November 22, 1949, and 128,917, filed Nothis was a larg r harge h n in Ex mple w vember 22, 1949, we have described the chlorohours were q d to d still o utra ity. Demethylation of certain aromatic nitro compounds Splte the longer f t0 v t d't mp raand the dichloromethylation of nitrotoluene, retur s the yield was still 85%.

spectively. Beginning with these compounds, we In a S lar manner, the following compounds have found that chlorine may be replaced by were prepared! other functional groups by reacting the nitro N compound with an alcohol or an alcohol ether of a polyhydric alcohol.

The following examples will serve to illustrate vpreferred embodiments of the invention but it omoomcmon is will be understood that the invention isnot limited thereto. B. P. 168-70" c. 0.5 mm.

Example I 3 NO, 765 parts by weight of ethylene glycol re j mixed with 103 parts by'weight of nitrobenzyl chloride. The mixture was rapidly distilled and the distillate tested from time to time for the 40 Hi0GHOH0CH=CH00m presence of hydrogen chloride acid as follows: i

9 B. P. 1744" C./1.5 mm.

, 1 Vol.0f hi0 Elapsed Time (Min.) B. P. Di ti l te H01 in Dist.

164 0 +(lst drop).

8g 1 i noomomocmcmocrnomon 192 128 197 168; 199 220 Weak+ 200 275. Neg. Not distillable NO: The remaining mixture was distilled under a water pump vacuum (about 12 mm.) and the residue distilled under a vacuum oil pump. Practically all of the liquid distilled as a golden yellow oil at C. and 0.3 mm. pressure, leaving CHOCHCHOHCHOH only a negligible residue. The yield was found V R 170.17? (3401105 CHiO CHzCHzO CHQ CHEOH B. P. 152-4 C./0.01 For the formation of the ethers, both :monohydric and polyhydric alcohols may be used as well as alcohol ethers of polyhydricalcohols.

examples of monohydric alcohols may be men-' tioned methyl, ethyl, propyl and butyl. "As examples of polyhydric alcohols may be mentioned ethylene glycol, trimethylene glycol and other methylene glycols, glycerol, and the higher polyhydric alcohols such as erytrithol, mannitoLsorbltol, etc. and the alcohol or partial ethers thereofsuch as the monomethyl, monoethyl and monowherein R. is the ether residue formed from com pounds :selected from the ;.group consisting of alcohol and alcoholethers of polyhydric alcohols,

X is selected from the group consisting of hydrogen and methyl, and Y .is selected-from the group consisting of hydrogen, chlorine and .the methyl ethers of alcohols and alcohol ethers of polyhydric alcohols.

2. A compound having the formula:

3. A compound having the formula:

HO CHrCHaO CH7- 'hutyl ethers of ethylene glycol and the monoethylethers of 1 diethylene glycol, etc. "Further examples of the nitro compoundswill be obvious .to

4. A method for preparing compounds having the following formula:

whereinRisthe,iether residue formed from compoundsselectediffrom the group consisting of alcohol and alcohol ethers of polyhydric alcohols,

,X is selected from the group consisting of hydrogen and-methyl, and Y is selected from the group consisting of hydrogen, chlorine and the methyl ethers of alcohols and alcohol ethers of polyhydric alcohols, which comprises reacting the corresponding chloromethyl compound with the corresponding alcohol .or alcohol ether and separatingthe compound by distillation.

5. The compound having'the formula,

cmoomcnlon 6-. A compound having-the formula,

CHzOGHz H'OH (3112011 .7. A compoundhaving the formula,

-omoomomoomomon 'SAULRJBUC. DAVID-I. REFERENCES CITED The. following references are of 'record in ithe file of this patent:

UNITED 1 STATES PATENTS rNumber Name .Date

2,450,277 Doelling et al. Sept. 28, 19448 2,485 .712 Doellinget al. Oct. 25, .1949

FOREIGN PATENTS Number Country Date 379,881 Germany Aug. 28, 1923 655,871 iFrance ..Apr. 24;, 1929 

1. THE COMPOUNDS HAVING THE GENERAL FORMULA: 